*Brock Fillinger took more than 40 JetBlue flights in 24 days. Photo courtesy of Brock Fillinger.*

It’s easy to recognize people doing the JetBlue 25 For 25 challenge, according to Brock Fillinger.

“They’re pretty easy to identify, because they’re the only people that are getting off of a flight, just milling about, then getting back on the same flight,” he said.

Fillinger, a Waltham resident, was laid off from his job at Verizon Business Group on Aug. 1, started the 25 For 25 challenge on Aug. 4 and finished on Aug. 27, taking more than 40 flights, including a test run of four flights. According to JetBlue, he was the 7th person to finish the challenge.

Flying to a city and then taking the same flight back to where you came from is perhaps the most efficient way to complete JetBlue’s 25th anniversary challenge, which involves flying to 25 unique airports between June 25 and Dec. 31.

Completing the entire challenge nets the challenger 350,000 TrueBlue points (a financial value of roughly $4500-$5000) and 25 years of JetBlue Mosaic 1 status. This status unlocks a whole host of perks, including twofree checked bags, preferred seating and priority security.

“This promotion lets us reward our most loyal customers, attract new members into the TrueBlue program and encourage exploration across our network,” said Ed Pouthier, JetBlues’s vice president of loyalty and personalization, in an emailed statement. “It’s exactly the kind of bold, fun, one-of-a-kind program that JetBlue became known for, and we’re proud to celebrate 25 years with such a valuable opportunity for our customers.”

The strategy

According to JetBlue, 31 people have completed the full challenge, including eight in the Boston area.

But 25 unique airports is a lot, especially when it comes to how JetBlue operates.

“The big [airline] carriers operate under a hybrid hub model, which is kind of how I thought all airlines operated,” said Fillinger. “In that you can go to Boston and you can go to San Francisco, and then San Francisco will connect to 10 or 15 places, and Denver connects to 10 or 15 places, and Atlanta connects to 10 or 15 places, or whatever it may be.”

JetBlue doesn’t work that way. As a younger regional airline that is just starting to transition into international and more domestic travel, it primarily operates out of three major hubs, according to Fillinger. The hubs are Boston Logan International Airport, John F. Kennedy International Airport in New York City, and Fort Lauderdale-Hollywood International Airport.

Initially, Fillinger figured he could ask a chatbot like ChatGPT or Google Gemini to find him the most efficient way to fly to 25 cities, but he was disappointed with that result.

“ChatGPT gave me a bunch of itineraries, as did Gemini, as did Google Flights, as did all the other ones that I had tried,” he said. “And they were all hallucinated. When you actually went and looked at the actual itinerary to validate it, it was making up the flights.”

So he decided that he would work out the most optimal path by himself.

As a student at Harvard Extension School for data science, Fillinger had been learning the Python programming language over the summer. He switched his final project for the class from a random game to a script that would find the most efficient way to complete the 25 For 25 challenge.

The program he wrote revealed that, while he could chain up to 18 flights in one go, it was much safer and more reliable to fly to a place from Boston and then fly right back on the same airline.

“If you’ve booked this sequence of flights, you end up getting really jammed up,” he said. “You might get trapped in a place where you might have to spend a lot more time rerouting to get back to your ‘plan of attack.’”

The there-and-back-again method, by comparison, was “smooth as butter” for Fillinger. After booking the flights, he didn’t have a single problem, outside of a sketchy experience in Presque Isle, Maine, which has only one flight per day, closes at night and has but one taxi driver to take travelers to and from the hotel 3 miles away.

As a frequent traveler, Fillinger had accumulated a massive amount of TrueBlue points that he used to complete the challenge, spending only around $400 of actual money.

He used around 480,000 points, got 10% back from his JetBlue credit card, and then received 350,000 points from JetBlue two days after completing the challenge, so he actually only spent around 85,000 points in total.

“When I figured out that they were going to give me all the points back, it’s like, well, it would be silly for me not to take all these flights, you know?” said Fillinger.

Discovering a community

One of the biggest impacts of the challenge for Fillinger was the discovery of the 25 For 25 community. “25ers,” as they call themselves, have taken over a JetBlue Reddit page to discuss the challenge, and there are multiple Discord forums dedicated to it.

In fact, on his first flight of the challenge, he met a 25er, one of about six or seven that he would run into over the course of the challenge.

She was retired, lived in New Hampshire and was on her sixth city. Her method was the exact opposite of Fillinger’s. She would take the bus to Logan Airport, walk up to the JetBlue flight counters, and ask what flights they had going to somewhere she hadn’t been before. She would then book the roundtrip.

“Complete opposites of how we were tackling this problem,” said Fillinger. “Mine’s analytical, hers is more adventurous. We’ve been comparing notes since then, we exchanged emails, and said ‘hey, have you tried this,’ ‘have you tried that,’ and that kind of microcosm has blown up into all of these groups where people are talking [about the challenge].”

Fillinger is still active in those spaces, offering advice to fellow 25ers about methods, destinations and the effects the challenge has on a person, like the mental toll of flying for six or seven hours in a day just to end up back where you started.

The next steps for Fillinger now are completing school, which started up again at the beginning of September, and looking for a new job.

“I kind of used this as my brief mental break to accomplish something,” he said, “and now it’s basically, go do the same thing, take these skills that I have and go apply them to somewhere in the business world.”

From a travel standpoint, he and his wife are looking forward to experiencing JetBlue’s Mint seats, its version of first class. They would like to go to London or Dublin in the future.

After completing the challenge, Fillinger was looking over the flights he was on and he found something interesting.

His first challenge flight on Aug. 4 and his last flight on Aug. 27 were on the exact same plane, named “My Other Ride is a JetBlue A320” (in keeping with JetBlue planes’ names relating to jokes or puns).

And on that final flight to Pittsburgh, the captain got on the mic and announced that the plane would be retiring that weekend.

“I thought it was a very weird kind of circular,” said Fillinger.